Wow, lots of misinformation on road quality. As someone who lives in the Chicago area, I can tell you that the interstates that are toll roads in Northern Illinois are in much better shape than the ones that aren’t. I-90 for example, was just rebuilt between O’Hare Aiport and Rockford. Given your location I would recommend taking the Tri-State Tollway (I-294) around the city. Try to avoid morning and evening rush hours. It’s possible to avoid tolls completely and go through the city, but it would potentially be a lot slower with rougher roads.
FYI, IPass works anywhere EZPass is used and Illinois accepts EZPass. In Illinois you set up an online account. The Illinois Tollway Authority owns the IPass transponder, and you have to put down a deposit on it. I’d recommend searching around for the best deal.